- Synthesis method 5 - halogeno-veratraldehyde
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The invention belongs to the field of organic chemistry, and in particular relates 5 - to a method for synthesizing halogenated O-veratraldehyde by using 4 - halogenoylguaiacol as a raw material to obtain 2 -hydroxy -3 - methoxy -5 -halogenated mandelic a
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- A synthetic preparation method for small carbags hydrochloric acid
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The present invention belongs to the field of organic chemistry, relates to a method of synthesizing berberine hydrochloride, comprising: S1: with 5-halo-o-quinoastearaldehyde and piperine ethylamine to obtain N- [2-(3,4-dimethoxyphenyl-5-yl) ethyl] -1- (5-halo-2,3-dimethoxybenzyl) methylimide; S2: to obtain 2- (3,4-diimoxyphenyl) -N- (5-bromo-2,3-dimethoxybenzyl) ethylamine; S3: to obtain 2-(3,4-dimethoxyphenyl) -N- (5-bromo-2 S4: to obtain 12-halogenated berberine derivative; S5: to obtain berberine. The present invention is free from the application of the by-product o-vanillin synthesis of o-resveratal raw material constraints, synthesis of 5- substitute o-resveratal and piperine ethylamine, and the use of the two preparation of berberine hydrochloride, with raw materials readily available, mild reaction conditions, easy to operate, high chemical yield, low cost and other advantages.
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- Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach
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Lamellarin K is a complex pyrrole natural product and member of the lamellarin family – a group of natural products known for their potent biological activities, such as, antiproliferative activity and inhibition of P-gp mediated drug efflux pumps. We herein describe the synthesis of the N-benzyl-des-D ring analogue of lamellarin K using a route that centres on an acyl-Claisen reaction to eventually prepare a highly-functionalised 1-aryl-4-methyl-1,4-diketone. Paal-Knorr pyrrole formation using this diketone undergoes auto-oxidation to give a fully-substituted 5-formyl pyrrole which was converted into the natural lactone B ring. Antiproliferative testing of the N-benzyl-des-D ring analogue gave an IC50 of 2.63?μM against the MDA-MB-231 breast cancer cell line.
- Dittrich, Nora,Pilkington, Lisa I.,Leung, Euphemia,Barker, David
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p. 1881 - 1894
(2017/03/11)
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- Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A
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A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)2 and Bi(OTf)3 in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).
- Kakde, Badrinath N.,Kumar, Nivesh,Mondal, Pradip Kumar,Bisai, Alakesh
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p. 1752 - 1755
(2016/05/19)
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- Metal triflate-catalyzed cyclization of arylvinylcarbinols: Formal synthesis of (±)-dichroanone and (±)-taiwaniaquinone H
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A formal synthesis of diterpenoids viz. the taiwaniaquinoids (±)-dichroanone (1a) and (±)-taiwaniaquinone H (1b) possessing an all carbon quaternary stereocenter has been reported. The key step involves a metal triflate-catalyzed cyclization of arylvinylc
- Kakde, Badrinath N.,De, Subhadip,Dey, Dhananjay,Bisai, Alakesh
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p. 8176 - 8179
(2013/09/02)
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- In vitro affinities of various halogenated benzamide derivatives as potential radioligands for non-invasive quantification of D2-like dopamine receptors
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Benzamide derivatives as radiotracers have played an important role in diagnosing malfunction in dopaminergic neurotransmission. A variety of halogenated and two unsubstituted benzamide derivatives were synthesised and their in vitro affinities to dopaminergic, serotonergic and adrenergic receptors and their lipophilicities were determined. As references IBZM (3), raclopride (4) and FLB457 (5) were tested as well. The two iodinated compounds NAE (27) and NADE (28) displayed Ki values of 0.68 and 14 nM for the D2 receptor. The well-established radiotracers FP (1) and DMFP (2) showed affinities in the same range as did the brominated compounds NABrE (29) and NABrDE (30). The log D7.4 values of 2.91 for NAE (27) and of 2.81 for NADE (28) are in the range of those found for IBZM (3), FP (1) and DMFP (2). These facts allow to expect good properties for the two iodinated compounds NAE (27) and NADE (28) regarding in vivo imaging with SPECT.
- Stark, Daniela,Piel, Markus,Huebner, Harald,Gmeiner, Peter,Gruender, Gerhard,Roesch, Frank
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p. 6819 - 6829
(2008/03/27)
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- N-HYDROXYAMIDE DERIVATIVES POSSESSING ANTIBACTERIAL ACTIVITY
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Novel N-hydroxyamide derivatives are disclosed. These N-hydroxyamide derivatives inhibit UPD-3O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase, an enzyme present in gram negative bacteria and are therefore useful as antimicrobials and antibiotics. Methods of synthesis and of use of the compounds are also disclosed.
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- Improved specific radioactivity of the PET radioligand [11C]FLB 457 by use of the GE Medical Systems PETtrace MeI MicroLab
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[11C]FLB 457 is a high affinity dopamine D2 receptor radioligand that is used for visualisation and quantitation of extrastriatal dopamine D2 receptors with positron emission tomography (PET). In this study, we report a co
- Sandell, Johan,Langer, Oliver,Larsen, Peter,Dolle, Frederic,Vaufrey, Francoise,Demphel, Stephane,Crouzel, Christian,Halldin, Christer
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p. 331 - 338
(2007/10/03)
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- Bibenzyl derivatives from Pellia epiphylla
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Reinvestigation of the phenolic constituents from a diethyl ether extract of gametophytes of Pellia epiphylla yielded pellepiphyllin, 7- hydroxypellepiphyllin, perrottetin E, perrottetin E-11-methyl ether, 14'- hydroxyperrottetin E, 10'-hydroxyperrottetin E, 10'-hydroxyperrottetin E-11- methyl ether, 10,10'-dihydroxyperrottetin E and 13',13'''-bis(10'- hydroxyperrottetin E). The structures of three bisbibenzyls published earlier are revised. The new structures have been elucidated by two-dimensional NMR- techniques and chemical synthesis. In contrast to previous publications, pellepiphyllin has been found as a constituent of P. epiphylla.
- Cullmann, Frank,Becker, Hans,Pandolfi, Enrique,Roeckner, Eckard,Eicher, Theophil
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p. 1235 - 1247
(2007/10/03)
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- Ethynylation of aryl halides by a modified Suzuki reaction: Application to the syntheses of combretastatin A-4, A-5 and lunularic acid
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On treatment with trimethyl borate sodium acetylide undergoes a palladium-catalyzed cross coupling with functionalized aryl halides or triflates in reasonable to good yields. The ethynylarenes thus obtained serve as building blocks for the formation of the highly effective tubulin polymerization inhibitors combretastatin A-4 (1) and A-5 (2) as well as for the synthesis of the plant-growth regulator lunularic acid (36). VCH Verlagsgesellschaft mbH, 1996.
- Fuerstner, Alois,Nikolakis, Katharina
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p. 2107 - 2113
(2007/10/03)
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- 2-Phenyl-4-(aminomethyl)imidazoles as Potential Antipsychotic Agents. Synthesis and Dopamine D2 Receptor Binding
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A series of 2-phenyl-4-(aminomethyl)imidazoles were designed as conformationally restricted analogs of the dopamine D2 selective benzamide antipsychotics.The title compounds were synthesized and tested for blockade of YM-09151 binding in cloned African green monkey dopamine D2 receptor preparations.The binding affinity data thus obtained were compared against that of the benzamides and a previously described series of 2-phenyl-5-(aminomethyl)pyrroles.
- Thurkauf, Andrew,Hutchison, Alan,Peterson, John,Cornfield, Linda,Meade, Robin,et al.
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p. 2251 - 2255
(2007/10/02)
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- Facile preparation of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dimethoxy-5- (tributyltin)benzamide from isoremoxipiride: The precursor of [125I]- and [123I]epidepride
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[125I]Epidepride, (S)-(-)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-[125I]iodo-2,3- dimethoxybenzamide ([125I]NCQ 219), is a new, extremely potent radioligand, useful in the study of the distribution of the dopamine D-2 recepto
- De Paulis,Smith
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p. 1091 - 1095
(2007/10/02)
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- The Cyclisation of Benzylaminonitriles. Part 7. Regiospecific Formation of Methoxy-substituted Isoquinolin-4-ones using Methylthio Activating Groups
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Cyclisation of 3,4-dialkoxybenzylaminoacetonitriles proceeds preferentially through a spiro intermediate.A 2,3-dialkoxy analogue will therefore normally give a 5,6-dialkoxyisoquinolinone after rearrangement and 7,8-dimethoxy substitution is not obtained.I
- Gavin, James P.,Waigh, Roger D.
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p. 503 - 508
(2007/10/02)
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- Directed Synthesis of Translationally Isomeric -Catenanes
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In a multi-step reaction sequence the tetrahydroxymetacyclophane 12c is synthesized.Acetalisation with 1,25-dichloro-13-pentacosanone followed by nitration and reduction afforded the diamine 13c.By cyclization of this compound in 2-pentanol with sodium carbonate and sodium iodide under high dilution conditions the monomeric products 16, 17, and 18 are obtained in yields of 21.4, 7.7, and 0,9percent, respectively.On the basis of mass, 13C NMR and 1H NMR spectra the structure of these compounds is discussed.Starting from the precatenane 16 the -catenanes 25a,b,c and 26a,b,c are obtained in a multi-step reaction sequence.The structure of these compounds is confirmed by mass, 13C NMR, and 1H NMR spectroscopic investigations.
- Rissler, Klaus,Schill, Gottfried,Fritz, Hans,Vetter, Walter
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p. 1374 - 1399
(2007/10/02)
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- SYNTHESIS OF 6,7,2',3'-TETRAMETHOXY-5,4',6'-TRIHYDROXYFLAVONE
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6,7,2',3'-Tetramethoxy-5,4',6'-trihydroxyflavone and its positional isomers were synthesized, and any of them were not identical with the flavone isolated from Notholaena aschenborniana.
- Iinuma, Munekazu,Tanaka, Toshiyuki,Matsuura, Shin
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p. 2425 - 2428
(2007/10/02)
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- SYNTHESIS OF 5-HALOGEN-SUBSTITUTED 2,3-DIHYDROXYPHENYLACETIC ACIDS, THEIR ESTERS, AND 2,3-DIMETHOXYPHENYLACETOHYDROXAMIC ACIDS
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Many-stage general methods were developed for the synthesis of 5-bromo- or 5-chloro-substituted 2,3-dimethoxyphenylacetic acids from o-vanilin.Methods were also developed for their conversion into the corresponding hydroxamic acids, 2,3-dihydroxyphenylace
- Daukshas, V. K.,Martinkus, R. S.,Kuleshyus, V. A.,Shtel'bene, V. P.
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p. 458 - 463
(2007/10/02)
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